5 Ways I Grew My Freelance Business in 5 Years

Part 2: The Outer Build — How I Built a Sustainable Freelance Writing Business

Author’s note: This is Part 2 of a two-part series. If you haven’t read Part 1, you can find it here:
5 Powerful Truths I Learned 5 Years After Leaving Corporate America
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In June of 2021, I left Corporate America. I walked away from a steady paycheck, a clear career path, and the comfort of a structured environment. The first week was… intense. Forget about the brave-girl-walk-with-a-latte aesthetic. Day one of “self-employed” had me spiraling.

I think I lasted three hours at my desk before the seven-page to-do list I was working on triggered the first panic attack. There was nothing cute or motivational about the crippling anxiety I faced that first week. The overwhelming reality was that I had zero clients and zero income. (Seriously, thank God I had a supportive partner.)

Every single instinct told me I was being an absolute idiot. The ‘smart’ thing to do was accept the reality I’d worked SO hard for, climb the stupid freaking ladder, pocket the decent-enough paycheck, and just be happy-enough about it. That’s what a responsible adult would do.

As it turns out… I am not a responsible adult. At least, not by the world’s standards. And as it also turns out… I’m ok with that, because the world’s standards for 'success' do not work for me.

Everything in me was screaming that the only thing more “irresponsible” than quitting my reliable corporate communications job to be a professional freelance writer was to never give myself the chance to see how far I could go on my own terms.

So I pushed through the panic attacks and started working my way through the now 11-page to do list. Within a month, I landed a couple gigs, and within two months, I’d landed a few more. By the third month, the quiet, stubborn conviction had officially taken root. This was the right path. This was my path, and one way or another, I was going to make it work.

Fast forward five years, and I can say with confidence: I made it work.

It took me five years, but I’ve just about replaced the corporate income I left behind (almost to the dollar), and I built a stable freelance business without sacrificing my health, values, or peace of mind.

The growth I’ve experienced over the past five years hasn’t been flashy or dramatic. I don't have an overnight or '90-day' success story, but I’m totally ok with that. I chose to be deliberate. Careful. I wanted the steady route, and along the way, I discovered practical ways to grow a sustainable freelance business that were not only profitable, but deeply aligned with my core values.

Here’s how I did it…

5 Strategic tips for launching and growing a freelance business

1. Start with platforms that teach you the ropes.

I began my freelance journey on Fiverr, and honestly, it was the perfect place to start. Fiverr provided the ideal amount of structure, some income, and most importantly, a sandbox in which to learn. I learned how to communicate with clients, manage deadlines, scope projects, and handle the unexpected.

Every few months, I’d raise my prices, and the orders and the 5-star reviews kept coming. I was feeling really good, but within about 1.5 years, things started to plateau. Fiverr turned out to be an awesome set of training wheels, but not the foundation of my business. Competing on a global stage taught me the realities of freelance pricing, and it also made me realize that if I wanted to grow my income, I needed a more targeted approach.

Key takeaway

In the end, freelance platforms like Fiverr are excellent for learning, and you can make some decent money there. But if you really want to build something lasting, profitable, and uniquely yours, you’ll likely need to step beyond them.

2. Build systems and templates early.

As my second year of freelancing came to a close, I began to slowly transition away from Fiverr and instead focus on creating the backbone of my business: systems and templates. In other words...

I built a website, officially registered my business, developed proposals, templates, and invoices, crafted policies and workflows, standardized client communications, and determined what my clear expectations and delivery timelines would entail – including revision protocols.

It was impossible to think through and plan for every possibility, but I got my basic templates and workflows in place so I’d have something to lean on. Templates make life easier, and once you have them you can tweak as you go without reinventing the wheel for each client and project.

Another strategy that helped me get organized quickly was creating a menu – a clear list of services I was willing to provide and (perhaps equally important) the ones I wasn’t. Having that clarity and structure in place made it easy to say yes to clients and projects that were aligned and professionally decline opportunities that I knew weren’t a good fit for me.

My tools were simple and affordable but effective:

• Hostinger and Name Cheap for my website. (With Google Analytics, obv.)

• Microsoft 365 for drafting and delivering work in Word and PDF and PowerPoint for presentations and proposals.

• Canva for graphic design needs.

• Mail Chimp for my newsletter.

• PayPal for invoicing and financials. (Pro tip: When it's time to file taxes, you need to report 'gross income' and then expense the transaction fees.)

Key takeaway

Legally register your business. Registering my business with the state gave me legal legitimacy. (That was an AWESOME day! 🤩)

As an official business, I’m able to track expenses against income, take advantage of applicable deductions, and if/when the time comes, I’m in position to hire help in a professional, compliant way.

My newsletter keeps my community engaged. My blog helps with SEO, AIO, and demonstrates credibility. I network at professional associations and events where ideal clients are already present. I’ve hosted workshops, given presentations, and appeared on podcasts — all of which continue to generate leads and income years later.

And here’s what really surprised me… There are many businesses who care about keeping their copywriting human and ethical, and they’re willing to pay a personable, reliable, trustworthy, professional human to provide expert copywriting.

All this to say, I am SO glad I invested my time in relational funnels instead of digital ones. Relational alignment matters, and I’ve said no to clients and projects that didn’t feel right. Saying no isn’t easy, but it preserves your energy, professionalism, and integrity.

Key takeaway

Especially in this digital age of AI and Chat GPT, focus on a human-to-human business model. Competition will always be fierce, but real-life, in-person connections and word-of-mouth testimonials will always be more authentic and compelling than digital funnels. The more virtual the world becomes, the more people value real relational trust.

5. Build on momentum and keep going.

Growth hardly ever follows a straight line, and it rarely comes from a perfect plan or to-do list. But when you show up consistently, maintain your systems, and prioritize intentional effort in the right direction, opportunities, projects, and solutions naturally unfold.

There were so many times I felt like I had to ‘scramble’ to get in position for a new opportunity, but I didn’t let a lack of structure stop me from capitalizing on the moment. I didn’t wait to feel 'prepared' or have a 'perfect' blueprint for every step. I started before I was ready, sent the email before I perfected it, and then learned and adjusted as I went. I did my best to overdeliver for every client and just kept moving – one intentional step at a time.

At first, persistent momentum felt like foolish confusion or blind faith. But over time, the dance became familiar, and it didn’t demand as much energy. The lead magnet came together, the newsletter launched, the proposals were finetuned, the consultations turned into booked projects, and one blog idea always ended up turning into two or three more.

Key takeaway

Over time, intentional momentum will enable you to grow a sustainable and profitable business – one that continues to evolve in a way that feels aligned with who you are.

A note for aspiring freelancers

You do not need to tell social media what you’re doing. Just start doing it. You don’t need a flashy launch, viral social media content, or an instant six-figure success story to become a “successful” freelance writer. Sustainable growth doesn’t always follow hype, so... honestly? Forget the hype. You don't need it. Hype will NOT 'motivate' you; it will only stress you out.

The fact is freelancing isn’t glamorous, and vanity metrics will only distract you and slow you down. Instead of spending hours on a reel, prioritize consistency and professionalism, and when you receive an aligned opportunity, overdeliver.

Structure your goals, build momentum, and focus on good project management. Be consistent and selective and choose opportunities, clients, and projects that are actually a good fit for who you are and the value you offer.

In the end, growth is the natural result of unwavering perseverance, and real unwavering perseverance is deliberate, thoughtful, and often way more quiet than you'd expect.

The bottom line

If you crave real growth that lasts, disappear for a bit. Put your head down, delete social media, turn off Netflix, and just get to work. Concentrate, breathe, and keep taking the next aligned step. Eventually, your systems will get polished. Referrals will find their way to you, and you’ll have the self-sustaining, successful business of your dreams.

The past 5 years have been quite a journey, and I’m nowhere close to ‘done.’ If you want to keep in touch, learn from the lessons I’ve uncovered, and get insights on how to build your own business on your own terms, I invite you to subscribe to my quarterly newsletter where I share reflections, strategies, marketing intel, tips, tricks, freebies, and behind-the-scenes stories.

As a thank you, you'll receive a free copy of the mindful marketing guidebook - a step-by-step peaceful marketing strategy for launching and growing your business. Discover what's included

3. Invest in knowledge and professional advice.

I’m a big believer that strategic investments in expertise pay off, and I consulted with a CPA. I wanted to ensure my business finances and process were set up correctly from the start, which saved countless headaches later. I also invested in some reputable continuing education programs and some certified online courses to bolster my professional experience and education.

(To be really honest, I don’t feel like I ‘needed’ this – because I was already entrenched in the current trends of marketing and copywriting. But I wanted marketable credibility, and updating my CEU’s demonstrated high value and showed prospective clients that my price points were justified.)

Key takeaway

Chances are, you don’t need to spend thousands of dollars chasing viral strategies or participating in masterclasses led by Instagram gurus. For me, what made a significant difference over time was investing in a few targeted professional enrichment courses and CPA insights.

4. Focus on relationship-first marketing.

Social media? Minimal. Over the last five years, I think I’ve only done around 10 business related posts. Among my favorite Rebekah-isms, my core business philosophy has always been:

The REAL you > The REEL you

Because the truth is ONE good referral is worth so much more than 100 or even 1,000 likes. Instead of curating my social media profiles, obsessing over vanity metrics, and building digital marketing funnels for strangers, I focused on:

1. Relationships and in-person networking

2. Producing high-value content

3. Overdelivering on projects